FI61027C - Foerfarande foer framstaellning av terapeutiskt anvaendbara alkanolaminderivat - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara alkanolaminderivat Download PDFInfo
- Publication number
- FI61027C FI61027C FI3789/73A FI378973A FI61027C FI 61027 C FI61027 C FI 61027C FI 3789/73 A FI3789/73 A FI 3789/73A FI 378973 A FI378973 A FI 378973A FI 61027 C FI61027 C FI 61027C
- Authority
- FI
- Finland
- Prior art keywords
- radical
- hydrogen
- formula
- ethyl acetate
- mixture
- Prior art date
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- -1 alkylene radical Chemical group 0.000 claims description 120
- 239000000203 mixture Substances 0.000 claims description 104
- 150000001875 compounds Chemical class 0.000 claims description 65
- 239000001257 hydrogen Substances 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 150000003254 radicals Chemical class 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000006239 protecting group Chemical group 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 239000002243 precursor Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000005277 alkyl imino group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 297
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 243
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 111
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 57
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 48
- 238000002425 crystallisation Methods 0.000 description 41
- 230000008025 crystallization Effects 0.000 description 41
- 239000002904 solvent Substances 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 32
- 230000002829 reductive effect Effects 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 239000007858 starting material Substances 0.000 description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 239000007787 solid Substances 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 14
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 229960001317 isoprenaline Drugs 0.000 description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
- 239000003208 petroleum Substances 0.000 description 14
- 235000006408 oxalic acid Nutrition 0.000 description 13
- 230000000903 blocking effect Effects 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 241000282326 Felis catus Species 0.000 description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 230000000747 cardiac effect Effects 0.000 description 5
- ANBZWDBEKOZNHY-UHFFFAOYSA-N ethanol;oxalic acid Chemical compound CCO.OC(=O)C(O)=O ANBZWDBEKOZNHY-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 4
- CAQZTSCRGMRSHX-TYYBGVCCSA-N (e)-but-2-enedioic acid;ethanol Chemical compound CCO.OC(=O)\C=C\C(O)=O CAQZTSCRGMRSHX-TYYBGVCCSA-N 0.000 description 4
- UCYJVNBJCIZMTJ-UHFFFAOYSA-N 1-(ethylamino)propan-2-ol Chemical compound CCNCC(C)O UCYJVNBJCIZMTJ-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 4
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229940124630 bronchodilator Drugs 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 238000007327 hydrogenolysis reaction Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 238000001802 infusion Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 3
- ZQQSYPZAPHRXRY-UHFFFAOYSA-N 1-hydroxyazetidine Chemical class ON1CCC1 ZQQSYPZAPHRXRY-UHFFFAOYSA-N 0.000 description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000674 adrenergic antagonist Substances 0.000 description 3
- 239000002876 beta blocker Substances 0.000 description 3
- 229940030611 beta-adrenergic blocking agent Drugs 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000002026 chloroform extract Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N iso-butene Natural products CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- DURULFYMVIFBIR-UHFFFAOYSA-N practolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 DURULFYMVIFBIR-UHFFFAOYSA-N 0.000 description 3
- 229960001749 practolol Drugs 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- JLIDRDJNLAWIKT-UHFFFAOYSA-N 1,2-dimethyl-3h-benzo[e]indole Chemical compound C1=CC=CC2=C(C(=C(C)N3)C)C3=CC=C21 JLIDRDJNLAWIKT-UHFFFAOYSA-N 0.000 description 2
- AWZHBDDTQUVXJK-UHFFFAOYSA-N 1-(2-aminopropyl)-3-phenylurea Chemical compound CC(N)CNC(=O)NC1=CC=CC=C1 AWZHBDDTQUVXJK-UHFFFAOYSA-N 0.000 description 2
- HCTDRZMGZRHFJV-UHFFFAOYSA-N 1-chloro-3-phenoxypropan-2-ol Chemical compound ClCC(O)COC1=CC=CC=C1 HCTDRZMGZRHFJV-UHFFFAOYSA-N 0.000 description 2
- ZULYWHOJRVBUJU-UHFFFAOYSA-N 2-aminoethylurea Chemical compound NCCNC(N)=O ZULYWHOJRVBUJU-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 2
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000001871 Tachycardia Diseases 0.000 description 2
- PWUBONDMIMDOQY-UHFFFAOYSA-N acetonitrile;hydrochloride Chemical compound Cl.CC#N PWUBONDMIMDOQY-UHFFFAOYSA-N 0.000 description 2
- HKRONTUQBMLTMG-UHFFFAOYSA-N acetonitrile;oxalic acid Chemical compound CC#N.OC(=O)C(O)=O HKRONTUQBMLTMG-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical group 0.000 description 2
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 229920001577 copolymer Chemical group 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 229960002179 ephedrine Drugs 0.000 description 2
- AIMCUTZXDCCWFQ-UHFFFAOYSA-N ethanol hydrate Chemical compound O.C(C)O.C(C)O.C(C)O.C(C)O AIMCUTZXDCCWFQ-UHFFFAOYSA-N 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000000401 methanolic extract Substances 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 2
- WHCBCOGNYOBFIL-UHFFFAOYSA-N n-(2-aminopropyl)-2-phenylacetamide Chemical compound CC(N)CNC(=O)CC1=CC=CC=C1 WHCBCOGNYOBFIL-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000006794 tachycardia Effects 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 230000001052 transient effect Effects 0.000 description 2
- NVLRFXKSQQPKAD-UHFFFAOYSA-N tricarbon Chemical class [C]=C=[C] NVLRFXKSQQPKAD-UHFFFAOYSA-N 0.000 description 2
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- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
- IGIJDAVPCAUGCU-UHFFFAOYSA-N n-(1-aminopropan-2-yl)acetamide Chemical compound NCC(C)NC(C)=O IGIJDAVPCAUGCU-UHFFFAOYSA-N 0.000 description 1
- CAEALSAPHDTRRY-UHFFFAOYSA-N n-(2-aminoethyl)-2-phenoxyacetamide;hydrochloride Chemical compound Cl.NCCNC(=O)COC1=CC=CC=C1 CAEALSAPHDTRRY-UHFFFAOYSA-N 0.000 description 1
- OFNOTKBTVZPDMU-UHFFFAOYSA-N n-(2-aminoethyl)-2-phenylacetamide;hydrochloride Chemical compound Cl.NCCNC(=O)CC1=CC=CC=C1 OFNOTKBTVZPDMU-UHFFFAOYSA-N 0.000 description 1
- WYZXJFFDMNRBEP-UHFFFAOYSA-N n-(2-aminoethyl)cyclopentanecarboxamide Chemical compound NCCNC(=O)C1CCCC1 WYZXJFFDMNRBEP-UHFFFAOYSA-N 0.000 description 1
- SFOOQDKGASYPRW-UHFFFAOYSA-N n-(2-aminoethyl)cyclopentanecarboxamide;oxalic acid Chemical compound OC(=O)C(O)=O.NCCNC(=O)C1CCCC1 SFOOQDKGASYPRW-UHFFFAOYSA-N 0.000 description 1
- DTSMHNPPSHGIAA-UHFFFAOYSA-N n-(2-aminoethyl)methanesulfonamide;oxalic acid Chemical compound OC(=O)C(O)=O.CS(=O)(=O)NCCN DTSMHNPPSHGIAA-UHFFFAOYSA-N 0.000 description 1
- XETWPZRFZHJXAF-UHFFFAOYSA-N n-(2-aminopropyl)benzenesulfonamide Chemical compound CC(N)CNS(=O)(=O)C1=CC=CC=C1 XETWPZRFZHJXAF-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- ZDYUUBIMAGBMPY-UHFFFAOYSA-N oxalic acid;hydrate Chemical compound O.OC(=O)C(O)=O ZDYUUBIMAGBMPY-UHFFFAOYSA-N 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229960004321 pentaerithrityl tetranitrate Drugs 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
- 229960001999 phentolamine Drugs 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000005090 tracheal smooth muscle Anatomy 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C275/14—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5797072 | 1972-12-15 | ||
| GB5797072 | 1972-12-15 | ||
| GB4347873 | 1973-09-17 | ||
| GB4347873A GB1455116A (en) | 1972-12-15 | 1973-09-17 | Pharmaceutical compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI61027B FI61027B (fi) | 1982-01-29 |
| FI61027C true FI61027C (fi) | 1982-05-10 |
Family
ID=26265164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3789/73A FI61027C (fi) | 1972-12-15 | 1973-12-11 | Foerfarande foer framstaellning av terapeutiskt anvaendbara alkanolaminderivat |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US3928412A (ja) |
| JP (1) | JPS5919090B2 (ja) |
| AR (2) | AR213930A1 (ja) |
| AT (3) | AT345791B (ja) |
| BE (1) | BE808666A (ja) |
| CA (1) | CA1031362A (ja) |
| CH (4) | CH611876A5 (ja) |
| CS (1) | CS187389B2 (ja) |
| DD (1) | DD113349A5 (ja) |
| DE (1) | DE2362568C2 (ja) |
| DK (1) | DK158466C (ja) |
| ES (1) | ES421538A1 (ja) |
| FI (1) | FI61027C (ja) |
| FR (1) | FR2210407B1 (ja) |
| GB (1) | GB1455116A (ja) |
| HK (1) | HK24480A (ja) |
| HU (1) | HU169087B (ja) |
| IE (1) | IE38602B1 (ja) |
| IL (1) | IL43795A (ja) |
| IN (1) | IN139418B (ja) |
| KE (1) | KE3030A (ja) |
| LU (1) | LU68997A1 (ja) |
| MY (1) | MY8100035A (ja) |
| NL (1) | NL179203C (ja) |
| NO (1) | NO138335C (ja) |
| SE (1) | SE408794B (ja) |
| SU (2) | SU576917A3 (ja) |
| YU (2) | YU40097B (ja) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4038313A (en) * | 1970-01-08 | 1977-07-26 | Ciba-Geigy Corporation | Cycloalkylureido phenoxy propanolamines |
| US4167581A (en) * | 1972-12-15 | 1979-09-11 | Imperial Chemical Industries Limited | Alkanolamine derivatives and pharmaceutical compositions and uses thereof |
| US4171374A (en) * | 1972-12-15 | 1979-10-16 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
| US4034112A (en) * | 1973-06-22 | 1977-07-05 | Imperial Chemical Industries Limited | Ethanolamine derivatives having β-adrenergic blocking activity |
| US4117157A (en) * | 1973-06-22 | 1978-09-26 | Imperial Chemical Industries Limited | Ethanolamine derivatives having β-adrenergic blocking activity |
| US4041074A (en) * | 1973-07-19 | 1977-08-09 | Imperial Chemical Industries Limited | 1-Hydroxyaryl-2-amidoalkylaminoethanol derivatives |
| GB1573359A (en) * | 1977-12-20 | 1980-08-20 | Ici Ltd | Alkanolamine derivatives |
| US4041075A (en) * | 1973-12-12 | 1977-08-09 | Imperial Chemical Industries Limited | Phenoxy-alkanolamine derivatives |
| AT334385B (de) * | 1973-12-20 | 1976-01-10 | Chemie Linz Ag | Verfahren zur herstellung von neuen phenoxypropylaminderivaten und deren salzen |
| US4141987A (en) * | 1974-06-05 | 1979-02-27 | Imperial Chemical Industries Limited | 1-Aryloxy-3-thenamidoalkylamino-2-propanol derivatives |
| GB1521471A (en) * | 1974-06-05 | 1978-08-16 | Randall & Son Ltd J | Token-deposit locks |
| US4162331A (en) * | 1975-06-17 | 1979-07-24 | Nippon Shinyaku Co., Ltd. | Substituted N-(carboxymethyl)-3-aminopropan-2-ol derivatives |
| GB1540463A (en) * | 1976-10-07 | 1979-02-14 | Ici Ltd | Alkanolamine derivatives |
| IE47053B1 (en) * | 1977-05-23 | 1983-12-14 | Ici Ltd | Cardiac stimulants |
| US4172150A (en) * | 1977-05-23 | 1979-10-23 | Imperial Chemical Industries Limited | Cardiac stimulants |
| US4219561A (en) * | 1977-09-22 | 1980-08-26 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
| US4239700A (en) * | 1978-10-10 | 1980-12-16 | Texaco Development Corp. | Isatoic anhydride derivatives and use as chain-extenders |
| US4281189A (en) * | 1979-09-06 | 1981-07-28 | Hoffmann-La Roche Inc. | Sulfonamide intermediates for adrenergic blocking agents |
| US4301300A (en) * | 1979-09-06 | 1981-11-17 | Hoffmann-La Roche Inc. | Sulfonamide intermediates for adrenergic blocking agents |
| FR2477537A1 (fr) * | 1980-03-07 | 1981-09-11 | Francaise Sucrerie | Nouvelles guanidines acylees, urees et urees substituees, leur procede de fabrication et leur application en tant que medicaments |
| FI76551C (fi) | 1980-11-06 | 1988-11-10 | Sandoz Ag | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 3-aminopropoxifenylderivat. |
| DE3270905D1 (en) * | 1981-12-17 | 1986-06-05 | Haessle Ab | Para-substituted 3-phenoxy-1-carbonylaminoalkylamino-propan-2-ols having beta receptor blocking properties |
| CH653670A5 (de) * | 1983-03-03 | 1986-01-15 | Hoffmann La Roche | Benzamid-derivate. |
| US5238962A (en) * | 1983-03-03 | 1993-08-24 | Hoffmann-La Roche Inc. | Benzamide derivatives |
| US4593039A (en) * | 1984-04-02 | 1986-06-03 | Merck & Co., Inc. | 1-aryloxy-3-(substituted aminoalkylamino)-2-propanols |
| DE3427309A1 (de) * | 1984-07-25 | 1986-01-30 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue 1-aryloxypropanolamine, verfahren zu ihrer herstellung und ihre verwendung |
| DE3512627A1 (de) * | 1985-04-06 | 1986-10-09 | Boehringer Mannheim Gmbh, 6800 Mannheim | Amino-propanol-derivate, verfahren zu deren herstellung, verwendung derselben und diese enthaltende arzneimittel |
| DE3687035T2 (de) * | 1985-05-14 | 1993-03-25 | William John Louis | 3-aminopropyloxyphenylabkoemmlinge, herstellung und arzneitmittel die sie enthalten. |
| EP0207036A1 (en) * | 1985-06-20 | 1986-12-30 | Aktiebolaget Hässle | New para-substituted 3-phenoxy-1-piperidinecarbonylaminoalkylamino-propanol-2-s having beta receptor blocking properties. |
| GB8607313D0 (en) * | 1986-03-25 | 1986-04-30 | Ici Plc | Pharmaceutical compositions |
| GB8607312D0 (en) * | 1986-03-25 | 1986-04-30 | Ici Plc | Therapeutic agents |
| PT88988B (pt) * | 1987-11-13 | 1993-02-26 | Glaxo Group Ltd | Processo para a preparacao de derivados da fenetanolamina |
| JP2004137284A (ja) * | 1997-06-17 | 2004-05-13 | Kaken Pharmaceut Co Ltd | ２−スルファモイル安息香酸誘導体 |
| GB0417802D0 (en) * | 2004-08-10 | 2004-09-15 | Novartis Ag | Organic compounds |
| CN106977426A (zh) * | 2017-05-27 | 2017-07-25 | 哈尔滨师范大学 | 一种腰果酚苯基脲及其制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3459782A (en) * | 1963-08-26 | 1969-08-05 | Boehringer Sohn Ingelheim | 1-substituted phenoxy-2-hydroxy-3-isopropylamino-propanes |
| GB1199037A (en) * | 1967-09-27 | 1970-07-15 | Ici Ltd | Alkanolamine Derivatives |
| GB1285038A (en) * | 1969-02-21 | 1972-08-09 | Ici Ltd | Alkanolamine derivatives |
| BE754604A (fr) * | 1969-08-08 | 1971-02-08 | Boehringer Sohn Ingelheim | Le 1-(2-nitrilophenoxy)-2-hydroxy-3-ethyl-aminopropane et ses sels |
-
1973
- 1973-09-17 GB GB4347873A patent/GB1455116A/en not_active Expired
- 1973-12-03 IE IE2183/73A patent/IE38602B1/xx unknown
- 1973-12-04 US US421669A patent/US3928412A/en not_active Expired - Lifetime
- 1973-12-04 CA CA187,289A patent/CA1031362A/en not_active Expired
- 1973-12-06 IN IN2664/CAL/73A patent/IN139418B/en unknown
- 1973-12-10 IL IL43795A patent/IL43795A/xx unknown
- 1973-12-11 FI FI3789/73A patent/FI61027C/fi active
- 1973-12-13 SE SE7316863A patent/SE408794B/sv unknown
- 1973-12-13 NL NLAANVRAGE7317096,A patent/NL179203C/xx not_active IP Right Cessation
- 1973-12-13 LU LU68997A patent/LU68997A1/xx unknown
- 1973-12-14 FR FR7344780A patent/FR2210407B1/fr not_active Expired
- 1973-12-14 CH CH1340377A patent/CH611876A5/xx not_active IP Right Cessation
- 1973-12-14 CH CH1759473A patent/CH605666A5/xx not_active IP Right Cessation
- 1973-12-14 AR AR251531A patent/AR213930A1/es active
- 1973-12-14 BE BE138894A patent/BE808666A/xx not_active IP Right Cessation
- 1973-12-14 DD DD175410A patent/DD113349A5/xx unknown
- 1973-12-14 DK DK681673A patent/DK158466C/da not_active IP Right Cessation
- 1973-12-14 NO NO4794/73A patent/NO138335C/no unknown
- 1973-12-14 CH CH1340177A patent/CH605667A5/xx not_active IP Right Cessation
- 1973-12-14 HU HUIE600A patent/HU169087B/hu unknown
- 1973-12-14 CH CH1340277A patent/CH605668A5/xx not_active IP Right Cessation
- 1973-12-14 SU SU7301981054A patent/SU576917A3/ru active
- 1973-12-14 YU YU3246/73A patent/YU40097B/xx unknown
- 1973-12-15 JP JP48141162A patent/JPS5919090B2/ja not_active Expired
- 1973-12-15 ES ES421538A patent/ES421538A1/es not_active Expired
- 1973-12-17 AT AT581577A patent/AT345791B/de not_active IP Right Cessation
- 1973-12-17 DE DE2362568A patent/DE2362568C2/de not_active Expired
- 1973-12-17 CS CS738727A patent/CS187389B2/cs unknown
-
1975
- 1975-08-26 US US05/607,995 patent/US4010189A/en not_active Expired - Lifetime
-
1976
- 1976-04-12 AT AT266376A patent/AT344144B/de not_active IP Right Cessation
- 1976-04-21 AR AR262359A patent/AR214288A1/es active
-
1977
- 1977-07-26 SU SU772504510A patent/SU695555A3/ru active
- 1977-07-29 AT AT566077A patent/AT351557B/de not_active IP Right Cessation
-
1980
- 1980-03-03 KE KE3030A patent/KE3030A/xx unknown
- 1980-05-08 HK HK244/80A patent/HK24480A/xx unknown
- 1980-11-03 YU YU2806/80A patent/YU42539B/xx unknown
-
1981
- 1981-12-30 MY MY35/81A patent/MY8100035A/xx unknown
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